Dave,
Lots of questions here. If you're doing it all yourself, you need to pay attention to your personal risk tolerance and goals, asset allocation, the markets, the economy, taxes, interest rates, global trends, value vs. growth, and a hundred other things. If you're really intersted in these things and you pay attention, this will help you in self-directed investing. Many people are very good at investing for themselves. If instead, you don't have the time or desire to follow these things, you probably should look into getting help. Find someone you trust to help guide you. Trust in this area is critical. Make sure the advisor understands your goals and needs.
Usually you will pay a flat fee for a money manager. Depends on how often they (or you) are trading in your account to determine if fee-based or per-transaction is right for you. Some money managers hold hundreds of positions in a managed account.
As an aside, my personal rule is that if I buy a stock, and it goes down "X" percent, I sell. (You have to define what "X" is for you, if you manage your own account!) Obviously I've missed something that the market knew, and I have a set sales point to preserve capital. I know many people that think "it will come back", but sometimes a stock may take years (if ever) to "come back". What opportunities did you miss while waiting for the comeback? Some stocks do recover, but I know people that are in the position you are with other stocks.
You have to ask yourself lots of questions regarding investing to see what is right for you, and no set of answers produces a "rule of thumb" that applies to everyone. You'll always hear these rules but it's important to remember, investing is never "one size fits all". Good Luck with your investing!
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